N-(4-Methyl-2-pyrid­yl)-p-toluidine

(Received 12 December 2009;accepted 30 December 2009;online 16 January 2010)

In the title compound, C13H14N2, the dihedral angle between the aromatic rings is 48.1 (1)° and the bridging C—N—C bond angle is 127.24 (12)°. In the crystal, intermolecular N—H⋯N hydrogen bonding about a center of inversion generates a hydrogen-bonded dimer.

Related literature

For the structure of N-(2-pyrid­yl)-4-toluidine, see: Fairuz et al. (2008).

Experimental

Crystal data

C13H14N2

Mr = 198.26

Monoclinic, P 21 /n

a = 10.9385 (11) Å

b = 7.5708 (8) Å

c = 13.4372 (14) Å

β = 95.246 (2)°

V = 1108.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.45 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEX diffractometer

6758 measured reflections

2528 independent reflections

1797 reflections with I > 2σ(I)

Rint = 0.024

Refinement

R[F2 > 2σ(F2)] = 0.043

wR(F2) = 0.142

S = 1.05

2528 reflections

143 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

2-Chloro-4-methylpyridine (1 ml, 0.01 mol) and p-toluidine (1.2 g, 0.01 mol) were heated for 4 h. The product was dissolved in water and the solution extracted with ether. The ether extract was dried over sodium sulfate. Evaporation of the solvent gave large blocks of dark brown crystals. The crystals, when the outer parts were removed, were colorless.

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.86±0.01 Å; its temperature factor was refined.

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